Toluene → HCID 71238582、化合物

HRID 1502194ノート

反応式

HRID 1502194 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=3)[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:9][CH:8]=3.[CH3:28][O:29][C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1.C1(C)C=CC=CC=1>C(O)C>[C:15]1([C:10]2[CH:9]=[CH:8][C:7]3[N:6]([C:21]4[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=4)[C:5]4[C:13]([C:12]=3[CH:11]=2)=[CH:14][C:2]([C:33]2[CH:34]=[CH:35][C:30]([O:29][CH3:28])=[CH:31][CH:32]=2)=[CH:3][CH:4]=4)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

5

反応物 3

HCID 1140TolueneHCID 201262(4-Methoxyphenyl)boronic acidHCID 71238684HCID 71238684、化合物

生成物 1

HCID 71238582HCID 71238582、化合物収率 67.4%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

The 3-bromo-6-phenyl-N-(4-methylphenyl)carbazole (3.20 g) and 4-methoxyphenylboronic acid (1.65 g) were added to a solvent mixture of toluene (30 mL) and ethanol (8 mL), followed by bubbling with nitrogen. Then, tetrakistriphenylphosphine palladium (150 mg) and 21.2% aqueous sodium carbonate solution (7.80 g) were added to the mixture, and the resultant mixture was refluxed under nitrogen flow for 3 hours. The mixture was diluted with toluene. The toluene layer was washed with water and dried and the toluene was evaporated. The residue was treated through silica gel column chromatography (eluent: toluene), to thereby obtain 2.30 g of 3-phenyl-6-(4-methoxyphenyl)-N-(4-methylphenyl)carbazole as colorless powder.

後処理

  1. customby bubbling with nitrogen
  2. additionThen, tetrakistriphenylphosphine palladium (150 mg) and 21.2% aqueous sodium carbonate solution (7.80 g) were added to the mixture
  3. temperaturethe resultant mixture was refluxed under nitrogen flow for 3 hours
  4. additionThe mixture was diluted with toluene
  5. washThe toluene layer was washed with water
  6. customdried
  7. customthe toluene was evaporated
  8. additionThe residue was treated through silica gel column chromatography (eluent: toluene)

出典と根拠

ORDレコード
ord-5e64ea5af9194a609770f27b1964e383
出典データセット
uspto-grants-2015_12
特許番号
US09206202B2

反応ノート

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